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P7742

Sigma-Aldrich

Prostaglandin G2

≥95% (HPLC), acetone solution

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About This Item

Empirical Formula (Hill Notation):
C20H32O6
CAS Number:
51982-36-6
Molecular Weight:
368.46
EC Number:
200-662-2
MDL number:
MFCD00036971
UNSPSC Code:
12352204
PubChem Substance ID:
329820316

Quality Level

200

Assay

≥95% (HPLC)

form

acetone solution

shipped in

dry ice

storage temp.

−70°C

SMILES string

CCCCC[C@H](OO)\C=C\[C@H]1C2CC(OO2)[C@@H]1C\C=C/CCCC(O)=O

InChI

1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI key

SGUKUZOVHSFKPH-YNNPMVKQSA-N

Biochem/physiol Actions

Aryl hydrocarbon receptor (AhR) ligand and activator of the AhR signal transduction pathway. Also shown to activate nitric oxide synthase (NOS) in rat brain synaptosomal membrane fractions.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319,H336

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

EUH066

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
055K1782
045K1186
104K2736
062K1772

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G Wu et al.
The Journal of biological chemistry, 274(14), 9231-9237 (1999-03-27)
Prostaglandin H synthase (PGHS) is a self-activating and self-inactivating enzyme. Both the peroxidase and cyclooxygenase activities have a limited number of catalytic turnovers. Sequential stopped-flow measurements were used to analyze the kinetics of PGHS-1 peroxidase self-inactivation during reaction with several
Structural characterization of a pentadienyl radical intermediate formed during catalysis by prostaglandin H synthase-2.
S Peng et al.
Journal of the American Chemical Society, 123(15), 3609-3610 (2001-07-27)
Olivier Boutaud et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(10), 7130-7135 (2002-05-16)
Acetaminophen has antipyretic and analgesic properties yet differs from the nonsteroidal antiinflammatory drugs and inhibitors of prostaglandin H synthase (PGHS)-2 by exhibiting little effect on platelets or inflammation. We find parallel selectivity at a cellular level; acetaminophen inhibits PGHS activity
The cyclooxygenase reaction mechanism.
Wilfred A van der Donk et al.
Biochemistry, 41(52), 15451-15458 (2002-12-27)
D Thompson et al.
Molecular pharmacology, 36(5), 809-817 (1989-11-01)
The mechanism of inhibition of prostaglandin H synthase (PHS) by eugenol was investigated using purified apoenzyme reconstituted with either manganese protoporphyrin IX (Mn-PHS) or hematin (Fe-PHS). Eugenol stimulated Fe-PHS activity at low concentrations and inhibited at higher concentrations, an activity
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